


The Good Boy’s Quintessential Guide to Nabbing a Bad Boy

by madam_lit_nerd



Category: Supernatural
Genre: Alternate Universe - High School, Bad Boy Dean Winchester, Breaking the Fourth Wall, Castiel POV, Dean POV, Drug Dealer Dean, Drug Dealer Dean Winchester, Jessica POV, M/M, Secret Relationship, Senior Castiel, Valedictorian Castiel, but pretty tame, castiel is over 18, kinda smut, oblivious POV, outside pov, pov: brady, somehow Brady is both the narrator but not the narrator
Language: English
Status: Completed
Published: 2020-05-24
Updated: 2020-07-06
Packaged: 2021-03-03 06:21:36
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 17,559
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24346438
Author URL: https://archiveofourown.org/users/madam_lit_nerd/pseuds/madam_lit_nerd
Summary: The story of how good-boy valedictorian Cas meets and falls in love with bad-boy dealer Dean, with each chapter told from a different point of view.Chapter 1: Brady doesn't care who his drug dealer screws, so long as he keeps Brady in the good stuff.Chapter 2: Cas knows this thing with Dean has to mean something, right?Chapter 3: Jess can see it: when Dean gets home in a really good mood, Cas comes to class the next day in a really good mood too. Coincidence?Chapter 4: By the end of our conversation, it was clear: I was fucked. (1st person Dean POV)
Relationships: Castiel/Dean Winchester
Comments: 20
Kudos: 172





	1. Brady's POV

Brady screeched up to the curb and threw his BMW into park. He leaned forward to peer out the windshield, but even with his wipers going at full, he could only see dim shapes through the downpour. 

Man, where the hell was this guy? He said he’d be here with the— a knock on the driver window made him yelp. With a frown, he lowered the window the bare minimum. 

“You got the stuff, Winchester?” he yelled to the man standing outside. 

“You got the money?” 

Brady stared at him pensively for a long moment, then nodded and slid the wad of bills through the narrow gap in his window. 

Like he would’ve done anything else, though. 

He needed this shit to keep focused on fall midterms. Even with the extra _help_ he’d gotten from that one guy and the generous donation his dad had made, his Stanford spot was on the line. He couldn’t afford another bad grade, not now.

The man slid a baggy through, dropping it into Brady’s lap. 

As the rain suddenly lessened, more of their surroundings became visible. Brady could finally see the trees surrounding the abandoned parking lot, the bus stop on the corner…his classmate standing under the bus stop’s canopy, staring straight at them. 

“Shit,” he muttered. It was that weird Novak kid, the one who never talked or smiled or showed any hint of a personality. 

One time Mr. Singer had asked him what his favorite color was. The dude had said brown. Who the fuck chooses _brown_ as a favorite color? It was the same color as mud and shit. As in, literal _shit_. 

Winchester’s gaze swung over to see what had caught Brady’s attention. “Who the hell is that?” 

“One of my classmates.”

Winchester frowned. “He gonna talk?” 

Brady shrugged. “I don’t know…I don’t think he ever actually _has_ talked. I mean, other than answering questions in class.” 

“I’ll take care of this,” Winchester said. “You get the hell out of here before anyone else sees us.” But then he pointed at Brady. “And stay the fuck away from Sammy.” 

Brady rolled his eyes, trying to come up with some witty comeback, but the man kept talking. 

“That kid’s gonna do big things some day, and I don’t want you fuckin’ that up.” 

“Sure, whatever,” Brady muttered then screeched away into the rain that had picked up again. 

—

When Brady saw Novak in Anatomy on Monday, the dude went white then blushed up to his hairline. He studiously avoided Brady’s gaze and kept his head down. 

Whatever the fuck Winchester had said to him, it had obviously worked. 

—

Brady slipped around to the back of the bleachers. Everyone was focused on the field, the game, so he knew he wouldn’t be missed for a few minutes. 

As he crept along, his gaze swept the deep shadows. He heard a soft gasp, followed by a low chuckle. As he moved closer, he realized that whoever it was, there was some heavy action going on.

“You like that, Sweetheart?” It was a voice that was passingly familiar. 

After a moment of deliberation, Brady risked whispering, “Winchester?”

“Oh shit!” 

Suddenly, Winchester was being shoved out of the shadows, his unbuttoned jeans doing little to hide his semi. 

“What?” he snapped. When Brady held out another wad of cash, Winchester snatched it away and tucked it into his back pocket. “Ok, we’re square. Now get the hell out of here.” 

As he spun to leave, Brady heard a quiet giggle from whatever girl waited for Winchester in the shadows. That sound alone seemed to wrap around the man and tug him back into the darkness.

—

Winter break rolled around. He was _supposed_ to spend it in St. Barts with his girlfriend Lillith’s family, but then she’d walked in on him and Ruby at Alfie’s party. Which meant the whole thing was off. 

His dad wouldn’t spring for a vacation, since that money had gone to Stanford as yet another generous donation after Brady got caught cheating. So he spent his break in Devon’s basement, smoking pot and playing CoD through again.

Sometimes he worried about what that green shit was doing to his dick. But when it ran out, he still called up Winchester for some more. 

Winchester’s voice was groggy when he answered. “What the hell, man? It’s three in the morning.” 

“Dude, I’m out. I need—”

Winchester interrupted him. “Fine, text me tomorrow.”

“No, now,” Brady whined. 

“I’m not getting outta bed for—”

“I’ll pay you double!” Brady offered. 

“No.” 

“Triple?” 

“No.”

“Dude, I will pay you _quadruple_ if you meet up with me now.”

A long pause, followed by a soft voice, then came Winchester’s, “Fine, meet me at the parking lot in fifteen.” Brady heard rustling as Winchester said, “Hand me my boxers, Sweetheart” to whoever was with him. 

“Fifteen minutes,” Brady promised. 

“If you’re not there at 3:17 on the _dot_ ,” Winchester spoke to him again, “I’m coming back home, and you’ll still owe me the quadruple.” 

Brady could hear the soft voice speaking to Winchester just before they hung up. 

When Brady pulled into the dark parking lot, it was only 3:14, so he had a few minutes to spare. He sat in his car, scrolling down Anna's TikTok, cause damn could that girl dance, until he heard the rumble of an engine. He looked up and squinted against the bright glare of the headlights. Whoever had been with Winchester during their call now sat in the passenger’s seat. 

As before, Winchester walked up to Brady’s window to make the exchange, tossing in a paper bag as Brady handed him the money. 

“Who you got in the car?” He asked without thinking. 

“None of your damn business,” Winchester growled. “Now get the hell out of here before I beat the shit outta you for annoying me.” 

Brady nodded and put the car in reverse, screeching backwards out of the parking lot. As he drove back past the lot, he could just barely see the outline of Winchester and his latest girl leaning intertwined against the car. 

—

By Valentine’s, him and Lillith were back together, mostly cause he could buy her nicer things than that dickwad Crowley. As if that pretentious little shit could ever afford long-term with someone like her. 

The night before Valentine’s though, he was feeling that old restlessness crawl up his spine. He couldn’t risk another go with anyone, cause Lillith would find out and break things off again. So he did the next best thing and called up Winchester. There was no answer, but the voicemail said, “For business inquiries, call Ash” and listed a number. 

When he met up with Ash in some back alley, the guy actually made him get out of his car. But he was much chattier than Dean ever had been, so Brady didn’t feel bad asking, “Where’s Winchester?” after the exchange had been made. 

“Aw,” Ash chuckled. “they went to do some romantic shit for the weekend.” 

Brady nodded, but then his mind finally registered that word _they_. “Wait, what?” 

“It’s Valentine’s, man!” Ash reminded him. 

“I know that, but I didn’t…I mean, he’s actually dating someone?” 

For the first time, Ash frowned and shook his head. “Look, it’s not for me to tell you Dean’s business.”

Brady rolled his eyes. “I just meant that he doesn’t seem the type to be in a long-term relationship.”

“I bet he doesn’t.” Ash’s smile slipped back into place. “He’s actually pretty good at puttin’ up that mean front, ain’t he?” 

“So he’s not actually mean?” Brady guessed. 

“Oh, Man!” Ash burst out with a laugh. “He’s mean as _shit_ if you’re on his bad side, but when it comes to…” he eyed Brady for a moment then continued, “You ever heard that whole ‘teddy bear on the inside’ or ‘wrapped around the little finger’? That’s Dean-o.”

“I never would’ve guessed,” Brady admitted. 

“And you never should, because I gotta tell you: just from your vibe, I can tell you’re probably on Dean’s bad side.” 

“Which means…”

“To you, he’s gonna be mean as shit,” Ash promised. He punched Brady in the bicep then climbed back into his car and drove away. 

—

The rest of the semester flew by in a blur. Over spring break, Brady finally got his vacation (courtesy of Lillith’s parents). He would’ve preferred St. Bart’s, but this time her family went to Switzerland. 

He barely passed his finals, but the third donation from his dad had finally sealed the deal on Stanford. 

Graduation approached, and he was surprised to learn that Novak had earned valedictorian. Apparently his whole “quiet student” bullshit hid quite a brain. Brady couldn’t wait to hear him stumble through his speech for graduation. At least there’d be something entertaining about all that sitting and standing and walking bullshit. 

But the entertainment never came, because Novak—or _Castiel_ , as the graduation brochure listed him (Yeah, with a name like that, no wonder he was so fuckin’ weird)—well, he never showed up. He wasn’t at graduation _at all_. So the salutatorian, some nerd from his math class, gave his speech instead. 

It wasn’t until later, when students and their families mingled on the school’s spacious front lawn, that Brady finally learned the reason for Novak missing. 

Sammy told it to his girlfriend Jessica while they were driving to the ceremony, who texted it to her lab partner Ruby as they found a parking space, who yelled it to her cousin Meg just before they walked into the auditorium, who whispered it to her “alphabet neighbor” Crowley during the commencement speech, who snapped it to his best friend Balth after they all filed back out, who had already posted it to his TikTok earlier that morning, where Lillith and dozens of others now watched with wide eyes. 

Balth laughed into the camera as he yelled, “That dumbass eloped! He fuckin’ eloped with Dean Winchester.” 

Inaias jumped into the frame behind Balth. “The fuck kind of after-school special is this?” he yelled.

“I honestly didn’t think he was serious!” Balth gasped out between his laughs. “Our valedictorian ran off with the town drug dealer!” 

And suddenly, so many things clicked into place for Brady. That blush way back in anatomy had been accompanied by the tiniest of smiles, the giggle under the bleachers had been a little low, as had the soft voice over the phone, and there'd been the careful way Ash hadn't given any kind of name or pronoun...

About time, isn’t it? Most of us figured it out in the second scene…or maybe even the first, because was there ever any chance of it going any other way?

First, there was that day in the pouring rain, when Dean offered to give Cas a ride home… and he’d learned just how sharp Cas’s wit really was. 

“You really said your favorite color was brown?” 

Cas had laughed, a pretty blush staining up his neck to his cheeks. “Yeah.” 

“But brown is the color of shit! Literal _shit_!” 

Even in that first ride, Cas had somehow ended up with Dean in the backseat, getting kissed so perfectly, so thoroughly, like never before. 

Then there’d been the football game, when Cas had snuck away from Anna and Balth to find Dean under the bleachers.

“I’m meeting Brady in a couple minutes,” Dean had warned breathily as Cas slipped his hand into the front of his boyfriend’s jeans.

“I think that gives us plenty of time, don’t you?” Cas had whispered as he yanked Dean into a hungry kiss that promised so much more.

He hadn’t meant to moan when Dean nipped at his neck, and he knew Dean probably hadn’t meant to be so loud with his rough, “You like that, Sweetheart?” 

It was all just _so_ perfect until Brady ruined it. 

With a laugh, Cas had shoved Dean out into the open, pants undone, semi clearly visible…and with a soft giggle, he’d pulled him right back in.

Oh, and don’t forget that late night call when Cas had told his parents he was staying at Balth’s, but had actually ended up in Dean’s bed, getting fucked within an inch of his life. He’d known then, as Dean kissed and cuddled him afterwards, that he really was in love with Dean Winchester. 

He’d also known that, given half the chance, he’d happily let Dean beat the shit out of Brady for waking them up at 3 in the morning. But even that could be forgiven, since it’d led to sex in the Impala in an abandoned parking lot. Plus what kind of dumbasses would they be if they turned down _quadruple the fuckin' price_.

And then there was the weekend away for Valentine’s. Dean usually set aside most of the cash for Sammy’s college tuition, but he’d used some of it to get them a cabin in the middle of nowhere…so Cas could be as loud as he wanted when Dean slammed into his prostrate again and again, taking him apart and putting him back together in so many varied, colorful, _wonderful_ positions. 

That one had been a little trickier to hide from Cas’s parents, but Crowley was more than willing to help cover things up…especially since Cas had agreed to cover for him too. If rumors ever leaked out that Crowley and Lillith were still fucking on the DL (with Brady footing the bills now) Castiel would provide the alibi. He really had no problem with it, cause Brady had been on his shit list ever since that whole 3-a.m.-phone-call debacle. 

And when Dean had taken him to St. Bart’s for Spring Break and popped the question as they lay panting into each other’s cooling skin, Cas’s answer had been immediate and sure: _yes_. 

With graduation and adulthood and college and responsibility staring him down, he hadn’t wanted to waste a single second of the time he had with Dean for the summer. So sure, he’d skipped graduation—he didn’t wanna give any speech anyways. 

Instead, he and Dean drove off toward…actually, it’s not really any of our fuckin’ business, is it? We just have to trust that, wherever they are, they’re both happy. 

We might be able to catch up with them in the fall when Cas starts at ASU, where he’ll be living in a nice apartment with Dean, who’s already gotten a job at the nearby auto shop. He doesn’t really need to sell anymore, not since Sammy earned a full-ride to two of his top three...not since Cas started looking at Dean like he hung the moon itself.

“I’m going legit,” he’ll say as he takes Cas’s hand in his, their matching engagement bands glinting in the Arizona sun.

It’s so adorable, it’s _sickening_.


	2. Castiel's POV

**Summary for the Chapter:**

> A retelling of the previous chapter, this time from our dear Cas's POV.

**Notes for the Chapter:**

> At first this was definitely just a one-chapter, outsider POV fic, but this morning I woke up with Cas's side in my mind. There are several shared scenes from chapter 1, but all are completely re-written from Cas's side (ie: I didn't just copy and paste those parts), but there are also a few new scenes that Brady would have never known about. 
> 
> So, I hope you enjoy this update! I'm kind of thinking I might do a couple more, like from Jessica's POV or even Dean's.

Castiel hated waiting for the bus on the best of days, but today, with the rain dumping down, sluicing over the top of the bus stop and splashing all over him...he really hated it. But life just wasn’t fair. 

He’d learned that a long time ago, when his dad had skipped out the back door and never come back. Then he’d relearnt it all over again when his mom had moved them across the country in the middle of Cas’s junior year to marry her internet boyfriend Chuck, who liked to pretend Castiel didn’t exist. Cause if Castiel didn’t exist, then neither did Naomi’s previous marriage. And Naomi seemed perfectly happy to pretend right along with her new asshole of a husband.

Cas hated that even more than the damn rain. That and the way he’d had to leave almost everything behind, even his VW. Now he had to catch the bus around town, rain or shine. 

All of his classmates at his richy-rich school had their BMWs and their...Lexuses? Lexusi? Who gave a fuck. All Cas knew was that they never got caught in the rain, never had to stand and wait for a smelly, dirty tube to transport them only half of the way home. 

Cas glanced over to the annex parking lot beside the library, usually abandoned at this time of day...or any time of day, actually. But today, there were two cars there. There was the silver BMW that Cas immediately recognized. It was that asshole Brady’s ride. 

God, that kid was a pain in the ass. 

Cas didn’t recognize the other car, though. The engine was loud, the paint black, the shape boxy. He didn’t remember ever seeing it in the school parking lot. 

He watched through the rain as a tall figure stood from the unknown black car and walked up to the BMW, leaning down to talk to Brady. Oh…. okay, that made sense. Everyone knew Brady was using...yes, everyone. If Cas knew, then that meant _everyone_ knew. Just then, the tall man stood up and looked straight at Castiel. 

_Oh, shit._

Cas immediately turned away, purposefully staring straight across the street. No need to make this day shittier with a beatdown from some fratboy drug dealer. 

He heard Brady’s car screech out of the lot. He knew it was Brady without even looking because he’d heard that same sound at the end of every school day for the past year. With a sigh of relief, he glanced over, expecting the black car to be gone too. He startled when he realized the tall man was only a couple feet away. 

“You Novak?” the man asked as he stepped under the shelter of the bus stop with Castiel. 

Cas meant to answer, he really did, but when the guy stepped closer, Cas could finally see him clearly. And hot damn, was he gorgeous. It took Cas a second too long to find his tongue again and make it work, but the man didn’t seem upset or impatient about that. 

“I don’t want any trouble,” he finally managed to stumble out. “I’m just waiting for my bus.”

“I can see that,” the man replied with a smirk. “I just wanted to offer you a ride.” 

Cas stared at him for a long moment, trying to gage if there was malicious intent behind the offer. 

The man held up his hands. “I promise, I’m not going to try anything.” 

Castiel really should have tried to stop the stupid words that popped into his brain, he really should’ve. He’d gotten really good at it in school, but there in the rain with that gorgeous man smirking down at him, he couldn’t seem to stop them. 

“Now don’t go promising that...I might want you to try a thing or two.” 

The man’s eyes widened, as if surprised, but then a slow smile spread across his face. “Well then, promise redacted.” He held out his hand. “I’m Dean Winchester.” 

Cas returned the smile. “Cas Novak.”

“Can I drive you home, Cas?”

Cas studied him for a long moment, pretending to mull over the offer, but he knew Dean could see right through him. Finally he nodded, and Dean spun to begin walking toward his car with Cas right behind. 

Once Cas had given Dean his address, they pulled onto the empty street. After a second of awkward silence, Dean glanced at Cas. “So, I’m a little confused. Brady said that you never talked, but not only have you talked to me, you’re actually pretty…” he paused to search for the word. 

“I am pretty,” Cas confirmed after a moment. “Or so I’ve been told.” 

Dean chuckled. “You’re _that_ right there.” 

“That right there?”

“Funny,” Dean finally supplied. “Smart. Sarcastic. Sharp.” 

“Brady thinks I don’t talk because he’s an oblivious asshole who only pays attention to whoever’s wearing the shortest skirt that week,” Cas supplied. “And no, nothing against girls wearing miniskirts, they can wear whatever the hell they want, but Brady’s a thirsty bitch.”

Dean laughed again. “A thirsty bitch?”

“When he’s not high as hell,” Cas confirmed. 

“So you know about the drugs?” 

Cas rolled his eyes. “Everyone does. But his daddy pays a lot of money to the school, so he doesn’t get in trouble for it.” 

“Ah,” Dean murmured. “So he’s oblivious when it comes to anything besides himself?”

“Well, not totally,” Cas admitted as they pulled to a stop at a light. “I overheard him once making fun of me for something I’d said.”

“What did you say?” Dean looked over at him, studying him closely, his green gaze dropping to Cas’s lips.

Cas smirked, even with the blush rising up his neck at the way Dean stared. “The math teacher, Mr. Singer, asked me what my favorite color was...I said brown.” 

A laugh burst from Dean, filling the car and wrapping around Castiel. It was the most honest, joyful sound he had heard in a long while. 

“You really said your favorite color was brown?” 

“Yeah.” 

“But brown is the color of shit! Literal _shit_!” 

Cas rolled his eyes. “Yeah, I was just being stupid. I assumed everyone knew I was being an idiot, but Brady doesn’t quite catch on to things like sarcasm.” 

Minutes later, Dean was turning the car onto Cas’s street. He pulled to a stop across from Cas’s house, and Cas could tell with a glance that his mom and Chuck were both gone. He looked back at Dean, blushing under that heavy green stare. 

“So, I think this is the part where I say thank you and get out?” 

Dean smiled, slow and predatory, and leaned in. “Only if you want to.” 

Cas didn’t need any more invitation than that. He practically threw himself at Dean, wrapping his arms around his neck. With the way their mouths crashed together, Cas knew that Dean was just as enthusiastic. 

Cas gasped when Dean shifted closer, out from under the steering wheel, and pulled Cas onto his lap. With a giggle, Cas rolled his hips, thrilled by the promising bulge he felt under him. The giggle was followed with an immediate “OW!” as he banged his head on the rearview mirror. 

“The back’s a lot roomier,” Dean promised between their next kisses. 

“Then what the hell are we doing up here?” Cas whispered. He hopped off of Dean’s lap and scrambled over the seat to the back, with Dean close behind. With a knowing smirk, the taller man laid himself out over Cas, bringing every bit of them in perfect alignment. 

The clothes stayed on, of course. No matter how handsome and funny and captivating Dean was, Cas wouldn’t want to go too far, not when they’d just barely met. But it was like Dean could sense this. He didn’t push, didn’t move any further than desperate kisses that invaded Cas’s hungry mouth and emptied his overactive mind. 

Minutes dragged by, the afternoon fading into evening as Cas and Dean kept exchanging whispers and gasps and more kisses. 

Finally, Dean pushed himself off of Cas and helped him sit up. 

“So, uh...I’ll see you around?” he offered. Cas smiled, that blush returning despite what they’d just been doing. 

“I certainly hope so,” Cas murmured, then he was out the door, running through the pouring rain to the still-empty house.

—

Cas saw Brady on Monday, and the sight of that pretentious asswipe reminded him of another face, another smile. He blushed as he thought of Dean. God, he really hoped that the guy had meant what he said about seeing Cas around. 

—

With a long suffering sigh, Cas trailed Balth and Anna into the football stadium. He hated sports—hated football especially—but they’d dragged him here with the promise to leave halfway through for pizza. As they walked past the back of the bleachers, he happened to glance over, and drew up short when he saw a familiar figure leaning there in the shadows—a familiar figure whose green gaze was locked right on Cas. 

Suddenly, he wasn’t quite so upset to be here. He waved, and Dean waved back, but neither moved forward. Cas would sneak away once Anna and Balth were busy watching the game. That seemed to be the norm for him and Dean now, anyways, sneaking moments of hungry kisses and playful banter into their busy lives. 

Cas felt like this all meant something, it had to. He was about 80% sure that this thing with Dean was solid. 

Once Balth and Anna were engrossed in the game, Cas muttered something about the bathroom and scurried away, slipping around the back of the bleachers to where he’d seen Dean. 

He walked slowly, his eyes scanning the shadows, until an arm slipped out of the darkness and tugged him in. 

“Hey,” Dean breathed before Cas’s mouth collided with his. 

“Hello,” Cas whispered back before their next kiss. 

They’d gone further and further each time, so Cas felt completely comfortable, confident even, as he reached down to toy with the button of Dean’s jeans. 

“I’m meeting Brady in a couple minutes,” Dean warned.

Cas slipped his hand into the front of Dean’s pants, giving a squeeze to the bulge he found there as he whispered, “I think that gives us plenty of time, don’t you?” 

The minutes slipped away, neither of them paying much attention to the world around them. Cas continued rubbing at Dean’s half-hard cock as his boyfriend (right, boyfriend?) bent down to nip at the nape of his neck. 

Cas gasped, sharp and loud in the silence behind the bleachers. 

“You like that, Sweetheart?” Dean growled, and Cas moaned. He _loved_ it when Dean called him that. 

“Winchester?” a voice called out. 

“Oh shit!” 

Dean struggled to get himself tucked back in, but then Cas, laughing wickedly, shoved him out into the open, fly still undone, to face Brady. 

“What?” Dean snapped. Silence, then Dean spoke again. “Ok, we’re square. Now get the hell out of here.”

The front he presented to Brady, and probably his other clients, was so different than what Cas got to see. With them, Dean was a tough-as-nails, beat-the-shit-outta-you drug dealer. With Cas, he was just as sharp, but in a much different way, a way that complemented Cas’s sharpness. 

Cas giggled at the put-upon tone, and Dean turned to smile at him, even as he returned to Cas’s ready arms and whispered, “You’re gonna be in so much trouble for that.” 

“Promise?” Cas giggled again as Dean leaned down to attack his neck with fresh nips and bruises. 

—

Cas walked down the hallway the next day in a slight daze, still thinking about his time with Dean the evening before. 

“That’s quite a collection you’ve got under that collar,” a voice called out, and Cas turned to find Crowley standing by the drinking fountain. 

“What would you know about it?” Cas goaded.

Crowley smirked. “Oh trust me, I’ve heard all about the Winchester special from Lilith and Ruby and...Meg, I wanna say?” Cas could feel his good mood faltering even as Crowley continued. “I mean, I was a little surprised when I realized it was you under there with him, since I never thought he ran our way.” 

Cas arched a brow. 

“The rainbow, love.” 

Right, Crowley was pansexual, as Cas well knew.

“We’ve just been...hanging out.” Cas tried. 

“I know, I know," Crowley soothed. "But be careful. He gets bored easily, just ask the others.” He jerked his head toward where Lilith stood with Brady’s arm around her, Meg and Ruby chatting with them. 

“Do they know?” Cas asked lowly. 

Crowley shook his head. “No, I just happened to be in the right place at the right time. I haven’t told.” 

“Wait, how do they even know him?” 

“He graduated, like, two years ago,” Crowley responded.

Right, before Castiel and his mom had moved here, back when she and Chuck were still just smiling pictures on a dating site. 

Cas smiled, hoping it didn’t look too sad. “Thanks. I’ll uh...I’ll keep it in mind.” 

“I just don’t want you hurt, love,” Crowley promised, and Cas could see that he really meant it. Even though they’d been broken up for a few months now, they still wanted what was best for each other. 

Cas glanced back to Lilith, then back to Crowley. He halted when he realized that Crowley was staring at her at her a little too intently. 

“You gonna go for it?” He asked. 

“No, she’s still with that bag of dicks.” 

Cas smirked. “I think I can take care of that.” 

He took off down the hall to catch up with Ruby, who’d started walking toward their literature class. He hooked her by the elbow as he caught up. 

“Castiel,” she greeted, not surprised in the least. 

“Ruby, we’ve always helped each other out, right?” 

Ruby nodded, obviously intrigued, but silent. 

Cas smirked. “You wanna do me a favor this weekend, at Alfie’s party?” 

“What’s in it for me?” 

“We finally get to rid Lilith of that human garbage can she’s dragging around.” 

Ruby smirked, “I like the sound of that. What else?” 

“I’ll owe you a favor,” Cas promised as they stepped into Ms. Mills’ room. 

With a hum, Ruby nodded. She slumped into her usual seat, near the back but not in the very very back, and Cas took his seat next to her. 

“Or,” she spoke up again, “I can just give you a little piece of advice.” 

Cas arched a brow at her. “Yes?” 

She leaned forward, her voice low. “Be careful with Dean,” she murmured. “He’s not really one to…” she trailed off at Cas’s panicked expression. 

“How do you know?” he whispered. 

She held up a finger. “I saw you wave at him, when we were all walking in.” She held up another finger. “You were gone for a very long time in the second and third quarters of the game.” She held up a third finger as she gestured toward his neck, “And that shirt doesn’t completely hide everything.” 

Cas glanced down, then realized he couldn’t actually see his own neck here in class. 

“Trust me,” she said. “I know from personal experience: Dean always goes for the neck, and he always moves on fast.”

“I know,” he replied. “Crowley was just tell—”

The bell rang, cutting off their conversation as they turned to face the front, but Cas couldn’t have recalled what Ms. Mills taught about that day to save his life. 

—

Jumping up and down while squealing excitedly, Gabe dragged Cas behind him. “Oh my god, this party is going to be so much fun! Don’t you just love Halloween?” 

Cas knew the other kids at school were envious of how he always got into the college parties. He kind of hated it, though. He was, at best, his idiot cousin’s babysitter for the night and designated driver for the times Gabe didn’t manage to talk his way into someone else’s bed. And somehow, with the Playboy Bunny costume Gabe wore, Cas knew he’d find someone tonight. 

“Yeah, it’s a real blast,” he agreed flatly.

He’d been in a mood since Tuesday, when Crowley and Ruby had talked to him. Even now, he could still feel the pain of their warnings. It was like his heart had shriveled up in his chest, curling into a tight little ball to protect itself from anymore hurt, and now it refused to relax. 

He’d begged off on the few texts Dean had sent, claiming homework, his parents, his goddamn _dog_. Dean hadn’t pushed too much after that, which meant that it was already happening. Dean was moving on. 

No sooner had they stepped inside, Gabe was running off to find Charlie, the host, and Cas was left alone. He wandered through to the kitchen, hoping to nab a soda, but stopped short. Dean was there, his arm flung around some girl in that Princess Leia bikini costume, laughing and smiling so openly at the others with them. 

So apparently that side of him wasn’t just for Cas. And apparently, the ending of Cas's whole thing with Dean wasn’t what _would_ happen; it had _already_ happened. Cas spun away and fled, back through the house, back out the front door, back down the street to Gabe’s car.

He didn’t really need to be in there in the party; he’d just wait until Gabe texted him the plan for that night. He climbed onto the hood of the small blue car and leaned back against the windshield, staring up at the empty night sky that was so unlike the star-filled skies of his hometown. God, he missed it so much right now, that simple little place where he hadn’t even met Dean, hadn’t ever experienced the man’s drugging kisses, hadn’t ever realized just how much he could care for another person like this, be hurt by another person like this. 

“Hey!” 

Cas’s thoughts froze. It was that familiar, deep voice that always sent his heart into overdrive.

He glanced up to find Dean walking towards the car. He tried to force a smile as the taller man climbed up onto the hood then crawled to straddle Cas’s waist. He brought his lips down to hover over Cas’s, a small smile playing at the edges.

“I’ve missed you this week.” 

“Had a lot going on,” Cas hedged. 

“But you’re here now,” Dean murmured. “Doesn’t seem like much going on out here.” 

“No, I guess not,” Cas agreed, finally letting Dean capture his lips. He didn’t kiss back though. Some part of him just...couldn’t. 

Dean pulled away, a frown tugging his brows together. “What’s wrong?” 

Cas tried to smile again, but it felt so tight and false. “What do you mean?”

“Why are you...” Dean trailed off. “Why aren’t you, you know, _participating_ here?” 

Cas sighed, refused to meet Dean’s eyes as he mumbled, “I guess my heart’s not in it.” 

Dean shifted back, just enough to study Cas’s face, but still remained in his lap. “This wouldn’t have anything to do with what you heard from Ruby and Crowley, would it?” 

Cas’s gaze shot to his. How the hell was it that everyone knew his business these days? 

“How?” 

Dean shook his head. “My kid brother Sammy...his girlfriend Jess overheard your little chat with Ruby.” 

“Oh…” 

“Yeah,” Dean smiled and leaned back in, bringing his lips so close to Cas’s again but not quite meeting them. “So when she came over and caught me moping around the house on Thursday, after you’d brushed me off _again_ with that bullshit excuse about your dog, she told me about it.” 

“Were they wrong? Crowley and Ruby, I mean.” 

Dean shook his head. “No, unfortunately not.” He finally dipped to capture Cas’s plush lips, smiling against his mouth, and this time Cas couldn’t help but respond. For long, silent moments their lips moved together, until Dean broke the kiss. “I’ve never once felt this way about anyone before.” 

“What way?”

“The way you make me feel, just by being here beside me.” He kissed Cas again then pulled back just enough to whisper, “Every time you laugh,” another kiss, “smile,” then another, “just fuckin’ look at me. I’ve never felt like this.”

Cas could feel the way his heart melted, the tight ball unfurling slowly with each word, each kiss. He knew that he was staring up at Dean like the man had hung the moon itself, but he could really care less about that when Dean dove in to capture his lips in a deep kiss, so hungry and desperate and _real_. 

“Do you really mean that?” Cas whispered after. 

“Of course I do!” Dean promised, his voice low and urgent. “Cas, I’m kind of scared to admit this, but I feel like...I feel like you’re it for me. I can feel it, every single time I look at you.” 

Cas’s smile was wobbly, his eyes damp. “I feel that way too.” 

“Which is so dumb, right?” Dean teased with a hoarse laugh. “I mean, I’m barely out of school, you’re still in your senior year. But…” He nuzzled his nose along Cas’s temple. “You’re just...you’re meant for me, and I'm meant for you. I can feel that.” 

Cas nodded. “I’m so sorry I didn’t ask you about it. I just...I assumed it’d hurt less if I just let it end now. And then I saw you in the kitchen with that girl.” 

“The girl dressed up as Princess Leia?”

Cas nodded, and Dean chuckled. “That’s Charlie, the host. She’s a lesbian. Not interested in this,” he gestured down to where his semi pressed tight against Cas’s, “not in the least.” 

“Good,” Cas muttered as his smile finally slid back into its place. “Because I am _very_ interested in it.” 

“Thank god!” Dean breathed as he brought his mouth against Cas’s. 

They didn’t do anything more than kiss. Cas didn’t think he could handle it, not with the way his heart had been so brittle all week. But even still, just sitting there with Dean, kissing and whispering and laughing, it seemed to stitch up that rip in his heart just perfectly. 

—

The first time Cas saw Jess after that Halloween party, he tugged her into a tight hug and thanked her for helping him and Dean.

“I had to do something!” she defended later as they ate lunch in the cafeteria. “I couldn’t bear to see either of you so sad.” 

By last hour, they were walking together to literature, muttering and complaining about Brady’s smarmy answers in anatomy. 

“Can’t be too mad at him, though,” Cas said. “He is kinda the reason Dean and I met.” 

He burst out laughing at her incredulous expression. “Yeah, I felt the same when I realized it.” 

“Realized what?” Sam asked as he came up on the other side of Jess. 

She wrapped her arms around Sam’s torso and frowned up at him. “Apparently _Brady_ is the reason Cas and Dean met.”

“Seriously?” Sam groaned, his expression conflicted. He stared out over the hallway for a long moment before looking back down. “But I can still despise him though, right?”

Jess’s smile was calculating. “I mean, sure...as long as you treat me and Cas to ice cream after our clubs.”

“Wait, what?!” Sam cried out, but at his girlfriend’s pleading expression, he just rolled his eyes. “Fine, I’ll think about it.” 

“And I’ll invite Dean,” Cas announced as he whipped out his phone, missing the fond smile that Jess and Sam shared. 

— 

It seemed inevitable, the way Jess immediately became one of Cas’s closest friends. Hell, his _best_ friend, closer than Castiel had ever been with any of his friends before, even back in Illinois. 

Then Naomi and Chuck announced their plans to fly to Boston for Thanksgiving, so Chuck could spend time with his kids. Naomi looked a little too relieved when Cas chose _not_ to go with them. He tried to ignore her relief and hide his own pain about it when he told Jess. 

She pulled him into a hug and softly reminded him of an obvious truth: even without Naomi, he’d always have somewhere to go. So Cas spent Thanksgiving Day at Dean’s instead. By the end of the day, with his heart and stomach full, Cas fell asleep curled into Dean’s side, feeling more loved and accepted than ever before. 

Only a couple weeks later, Christmas break had arrived. Even though Naomi and Chuck decided to stay in town, Cas found a way to sneak off to Dean’s. This time, though, Sam was at Jessica’s and Dean’s dad was who-knew-where, so they had the place to themselves. 

For the first time since their relationship had started, Dean and Cas went all the way. At first it was slow, deep, with Dean keeping his thrusts perfectly even and Cas letting out little half gasps. By the end, it was frantic, messy, with Cas crying out Dean’s name again and again as he came between their stomachs. 

After cleaning up, Dean cuddled him close and tight, whispering soft words into his temple. As Cas drifted away into sleep, he realized what that new glow in his heart was: _love_. He was in love with Dean, completely and irrevocably. 

Yes, he’d known that Dean was it for him since that Halloween party, but that word _love_ had loomed so big, he’d been afraid to accept it. Now, with each deep breath that tugged them further into sleep, he realized there’d been nothing to worry about. 

Well, almost nothing to worry about. Brady’s phone call in the middle of the night was upsetting, sure, but after Dean had thrown the bag of pot into Brady’s lap, he walked back to the Impala, to Cas. He tugged him out to sit on the hood with him, like they had at the party, but now at 3 in the morning with no lights and no other cars in the parking lot, Dean fucked Cas again right there in the backseat of the car, the very same spot as their first kiss. 

“Voyeurism,” Cas muttered as he caught his breath after. “Never would’ve guessed you were so kinky, babe.” 

Dean pulled back from the hickey he’d been working on and rolled his eyes. “Shut up and let me kiss you.” 

—

For Valentine’s, Dean kidnapped Cas right after school on Friday. He’d apparently worked out some excuse for Crowley and Balth to tell Cas’s parents, should they ever actually remember that Naomi still had a son in the home. 

Cas couldn’t tamper down his excitement, laughing and singing along to the radio as they flew down the interstate. 

When Dean pulled up to the secluded cabin he’d borrowed from Ash for the weekend, Cas gasped, threw his arms around his neck, and pulled his boyfriend into a long, heavy kiss. 

“You know,” Dean murmured as Cas finally broke for air, “it might be better to actually go inside the cabin, since it is ours for the weekend.”

Cas giggled, ready to follow Dean, but instead Dean scooped him up to carry him inside. 

For that entire weekend, Dean tugged Cas apart piece by piece, learning new things about him and his body that Castiel himself hadn’t known. Like how sensitive the inside of Cas’s thigh was, or how loud he got when Dean hit his prostate perfectly with every thrust. 

He adored Dean getting rough near the end, when his thrusts would turn uneven and haphazard. He adored Dean wrapping him up in his long, tan arms, fingers splaying low on Cas’s back to keep him close. He adored waking up in the morning to Dean’s smile, morning breath be damned. He adored showering with Dean, laughing as his boyfriend used the shampoo to twist their hair into funnier and funnier shapes. 

When Cas returned home on Sunday evening, backpack in hand, Naomi and Chuck were sitting on the couch, watching TV. They both seemed surprised to see him. 

“When did you go out?” Naomi asked. 

Cas shrugged. “A little bit ago. Had to go study with Balth.” 

“Okay, there’s leftovers in the fridge if you’re hungry.” 

Cas didn’t even feel angry, like he had before meeting Dean. He didn’t feel unworthy just cause his mom wanted to forget about her previous disaster of marriage. No, now he had Dean. Dean had shown him the truth in so many ways: he was absolutely worth every bit of love poured into him. 

—

A few weeks before spring break, Sam was awarded a hefty scholarship, so he convinced Dean to use some of the saved-up tuition money for a vacation with Cas. Sam (and Jess, when she could sneak away) stayed with the house while Dean and Cas flew down to St. Bart’s for the week. 

This time, Cas didn’t even make plans for if Naomi and Chuck discovered he was missing. Balth would know what to do. 

The week with Dean was perfect, from the sparkling beach to the fancy resort to the dark restaurants...but the most perfect part of all was their last night there. Dean lay curled around Cas, pressing small kisses along his shoulder, until he nudged Cas to turn over and look at him. 

Their gazes locked, and Dean smiled hesitantly. “I know we’re still young, and we’ve got a long way to go before this, but…” he trailed off, his eyes so wide and hopeful and vibrant. 

Cas realized what was happening, and he couldn’t stop the slow smile that spread across his face. “Ask me,” he whispered. “Please just ask me.” 

Dean’s smile matched Cas’s as he asked, “Will you marry me?” Before Cas could even answer, he was rambling on. “Not now, of course...but in a couple of years, maybe? Like, after we’re settled and ready and—”

Cas interrupted him with a kiss, giggling as he breathed his reply. “Yes.” 

Cas spent his last weeks of high school sailing on cloud nine down the halls. He hadn’t told anyone yet, of course, and Sam and Jess had both sworn to secrecy. 

About a week before graduation, he found out he’d won valedictorian, apparently much to Kevin Tran’s relief. The poor guy couldn’t speak in public for anything, which the valedictorian had to do....and that just made Cas feel worse when he decided to skip the ceremony, leaving Kevin to do the speech anyways. 

The morning of graduation, he slid into the passenger seat of the Impala, his smile wide and hopeful. 

“You sure about this?” Dean asked one final time. “I mean, it’d only be a couple hours wait to hit the road.”

Cas shook his head. “No, I’m sure. I want to spend every second possible with you.” 

Dean chuckled. He reached over to tuck Cas’s wild dark hair behind his ear. “God, I’m so glad I gave you a ride that day.”

“Me too,” Cas admitted. 

Dean flipped on the radio, ACDC blasting as the Impala roared down the street toward their future.


	3. Jessica's POV

**Summary for the Chapter:**

> Here, as promised in the notes last time, I have Jess's POV to the story. What's funny is...even though it's the same story with the same basic plot and events...there's no mention of Brady. So for any of you that were just done with his idiotic bullshit, he's never even mentioned here. 
> 
> Point of View is a crazy thing, huh???

The very first time Jessica met Sam Winchester in their sophomore biology class, she was a goner. Yeah, he was tall and lanky, and somehow both handsome and adorable at the same time. But what really caught her was his smile...it was almost as big as his face and so genuine. 

When Mr. Thompson paired them up for the lab for that year, Jessica knew it was the universe pushing her toward him. During that first lab with Sam, talking to him, listening to him speak, learning how passionate and smart and kind he was...it was a sealed deal. 

Yeah, her new friends at this new school warned her about his family. No-good drunk dad, drug-dealer older brother, long-gone dead mother (which, how the hell was that even something to hold against someone?) But even with all those warnings, she couldn’t stay away, because Sam… Sam was different. He had these big goals and aspirations—Stanford, law school, and beyond. He had dreams of helping and providing legal aid for poor communities. 

She did eventually meet Dean, of course. Yeah, he was a bit of a flirt, and it seemed he had a different girl passing to-and-from his bedroom each week. But she also saw how proud he was of Sam, how much hope he held for his future. Sam told her that every bit of money that didn’t go to essentials or bills, Dean set aside for Sam’s college fund. 

That’s why Dean had gotten into dealing, because no way in hell was John setting aside anything. And the way Dean saw it, people were going to find some way to get their drugs anyway, so why not jump into the business, earn as much as he could? He himself never used, and he kept that part of his life far away from Sammy and, subsequently, now Jess.

—

In that first year that she and Sam dated exclusively, she had to guess that Dean had anywhere between twenty to forty girls in and out of his room. She wasn’t judging him, of course. If that’s what made him happy, then that’s what made him happy. It seemed to be what he was looking for in life...until the next fall, the start of her and Sam’s junior year. 

She and Sam were sitting at the kitchen table as they worked on the mountain of pre-calc homework they’d already been given. 

“How was AP lit today?” Sam asked. Jess had managed to nab a spot in the senior AP lit class so she could clear her schedule for the internship option next year.

Dean wandered in just then to raid the fridge, tossing them a head nod as he passed. 

“Awesome!” she answered. “We talked about LGBTQ characters hidden throughout literature.” She chuckled. “A lot of very strong opinions, especially from Michael. Can you guess which side he took?” 

Sam rolled his eyes. “What a dick.” 

“Even Cas got really into it.” She smirked. “I think he was legit about to chuck th—”

Dean’s head suddenly popped up from the fridge. “You know Cas?” 

“Uh…” she glanced at Sam, who shrugged. “Yeah, he’s in my AP lit class. Really sarcastic, but in a funny way.” 

“Right?” Dean agreed with a grin. He grabbed the bag of grapes and allowed the fridge door to slam shut as he claimed a seat with them at the table.

Jess and Sam exchanged a look. Dean never sat with them. _Never_. He’d drive to the mall with them from time to time or even sit in on a movie night, sure, but otherwise he let them do their “gross couply thing” (as he put it).

“What’s he like?” he asked as he opened the bag of grapes. 

Jess arched a brow. “Cas?” 

He nodded and popped a grape into his mouth. 

“I mean, he seems really cool. He’s friends with, like, Balth and Ruby and Meg.”

“Inaias and Anna,” Sam added. 

“Yeah, that whole group,” she explained. She glanced back at Sam. “Right, he dated Crowley last year?” 

“Yeah, I think so. He’s in all AP classes,” Sam said. “Giving Kevin a run for his money.” 

Sam was too busy staring down at his textbook, but Jess was watching Dean. He had this little smile on his face, something she didn’t quite know how to interpret. If she had to guess...she’d say it looked a lot like the smile Sam wore when he was around her. But that couldn’t be right, because Dean was exclusively into girls. She’d never _once_ seen a guy in the mix. 

That little smile should’ve been her clue, though, because somehow she was still shocked when she found out. 

She was out for her usual evening run when she spotted the Impala parked on a narrow, practically deserted side-street. She knew it was Dean’s because he was the only one in town to own that car. She thought she might go up and say hi, but then she saw Dean in the backseat, obviously _with_ someone. 

She sped her running, trying to hurry past without drawing any attention from Dean or whoever else was with him, but at the last moment, another head popped up. It was Cas…

As soon as she was around the corner, out of sight of the car, she pulled out her phone to call Sam. 

He chuckled delightedly. “I wondered! I mean, he only brings him up every other day.”

The next time she saw Dean, she smiled apologetically. “I’m sorry! I know you were probably trying to keep it a secret—” 

He waved her off with a fond smile. “Nah, that’s more cause of Cas’s parents. They’re super conservative, you know?” 

“You seem to really like him,” she murmured, almost awed. She never, in a million years, would’ve pictured Dean in a steady relationship with anyone, much less a guy. But there was no denying his lovestruck look as he began gushing about how amazing Cas was, how funny, how smart. 

From then on, she paid more attention to Cas in their lit class. Nearly every time Dean was gone for the evening, the next day Cas would have the barest shadow of a bruise peeking out over the top of his collar, and the sweetest distant expression plastered on his face. He could still be sharp as ever, especially when Michael was going on about some stupid bullshit, but overall his aura seemed happier, more content. 

It was exactly the same as what she saw with Dean, and when she told Sam about it, he was relieved. He admitted one quiet night that he’d always felt guilty, because Dean was taking care of him, providing for his future. Now _Dean_ was happy, and maybe he’d found his own contentment, his own future. 

And then, just before Halloween, Jess was sitting in her usual seat, catty-corner to Cas’s, when she heard Dean’s name. She glanced up to find Ruby leaning in close to Cas, whispering something. Cas’s expression in that moment...it was devastating in its flatness. After weeks of gentle smiles and distant gazes and soft blushes, it was heartbreaking to see this old expression regain its place. 

Jess couldn’t hear the specifics of what Ruby was saying, but she could guess the gist, because Ruby had been one of Dean’s girls from the year before. And then Cas murmured in his low voice, “I know. Crowley was just tell—” 

The bell rang, and everyone shifted to look at Ms. Mills. The few times Jess managed to glance at Cas, her heart broke all over again. She wanted to hug him, to assure him that whatever Ruby and Crowley had said, that was the old Dean, the before-Cas Dean. But when class ended, Cas was out the door before she’d even managed to pack up her books. 

Should she tell Sam? Should she tell Dean? Should she even say anything at all? It wasn’t really her place to go meddling in her boyfriend’s older brother’s “secret” relationship, right? She’d run it by her sister later and try to get some advice. 

That night, she had a family thing, and the next she had to study for a big test, so the next time she was able to go over to Sam’s was Thursday. As soon as she walked in the door, she sensed the tension. 

“Dean’s been moping all night,” Sam muttered. “Apparently Cas has been avoiding him since the game on Mon—” 

Jess interrupted. “I know why!” 

Sam frowned as Jess leaned in to whisper about what she’d overheard, finishing with, “And I didn’t even know if I should say anything to Cas or Dean, because I didn’t want to start anything, you know?” 

Sam’s smile was understanding. “Don’t worry, I’ll talk to Dean about it.” 

“Talk to me about what?” Dean barked as he stomped toward the fridge. 

She exchanged a glance with Sam, who nodded encouragingly. Dean plopped down into the chair across from her, and her whole story spilled out. By the end, Dean was smiling again, this time a little ruefully. “Son of a bitch.” 

“Yeah?” Jess prompted. 

“I just...I thought he’d finally realized that he was too good for my dumbass.” 

Sam rolled his eyes. “Not true in the slightest, but okay.” 

Dean pulled out his phone, then paused. It seemed as if he was deliberating for a long moment, then shook his head. “In-person, it needs to be in-person.” 

“So go over and see him,” Sam encouraged. 

“He’s kind of avoiding me right now, Sammy.” Dean sighed. “Even if I did go over, there’s no way he’d come out to see me. I’d have to talk to his parents, which can’t happen because—” He dropped his head into his hands. 

Jess smiled and said in a sing-song voice, “There’s always this weekend.”

Dean’s head suddenly popped back up. “Is he going to that party? The big one at...I can’t remember his name.” 

Jess smirked. “No, but I did hear him talking about tagging along with his cousin Gabe to some college party.” 

Dean’s phone was back in his hand as he wandered out of the kitchen. 

She heard his voice carry from the next room, “Charlie, you got someone named Gabe goin’ to your party?” 

—

Jess had barely opened her locker on Monday when she heard a soft, deep “Hello, Jess” from beside her. She glanced over to find Cas standing there, the happy expression back in its place.

“Hey Cas!” she greeted. Before she could even ask, Cas was throwing his arms around her in a tight squeeze, then stepped back quickly. 

“Sorry, I…” He blushed, glanced down, then back up at her. “I just wanted to say thanks...you know, for talking to Dean. I know it couldn’t have been an easy decision to make, but I’m so glad you did.” 

“Of course!” Jess cried. “I couldn’t stand seeing you so sad, not when you’ve been so happy recently.” 

Cas arched a brow. “Huh?” 

“Um…” Jessica blushed at her unintentional confession. “It’s just...Dean is so happy now, and that makes Sam happy, and that makes me happy, and I can see it makes you happy too. Like, Dean would come home in a super good mood, and then the next day, you’d come into class in a super good mood, too.” 

Cas grabbed her arm, his smile splitting his face. “Please tell me _everything_.”

—

From then on, she and Cas were close, nearly inseparable...when Sammy and Dean weren’t around, of course. Actually, no, even then they hung out with the brothers by their sides. They still had their alone time, sure, but Sam was excited about how much time he got to spend with Dean now.

In class, she moved to sit next to Cas, and through him, Ruby on his other side. At first she was a little upset with the dark-haired girl, but after hearing the whole story from Ruby’s perspective, she realized that Ruby had just been trying to protect her friend. She found that she got along with Ruby so well, they decided to team up for their big project in Forensics the next semester. 

She’d also join Cas and his friends for lunch, with Sam tagging along, or Cas would come join them at their table. It was so easy to slip into friendship with him, because he was such a good soul who, even with this sarcasm and sharp wit, brought non-stop laughter to their lunches. 

But there were other parts she learned about that weren’t so good. 

She learned quickly how little regard Cas’s parents held for him, and it broke her heart. No wonder he’d always looked so miserable before. She saw for herself the times that Cas was overwhelmed, angry, heartbroken. But Dean...Dean seemed to heal that for him. More than once she watched as Dean led him from the house to take him for an ice cream or a walk, and by the time she next saw Cas, he was more content, more loved, than ever before. 

A week before Thanksgiving, Cas sat in her car before school, sobbing about how his mom hadn’t even cared when he said he wouldn’t go with them to Boston.

“Have you told Dean yet?” she murmured, and Cas shook his head.

“I’m always going to him about this, just throwing all my bullshit at him, and he doesn’t deserve that!” 

“He doesn’t think of it that way,” Jess assured him. 

“I know! My brain knows that, but my heart is just worried he’ll finally have enough and walk away!”

Jess pulled him into a hug, running a hand down his back. “I can promise you that is not the case _at all_ , hon.” 

The warning bell rang, and they left the warm car to trudge inside. Once Cas had gone down the hall toward his first hour class, Jess whipped out her phone and typed a short message to Dean. 

At lunch, Cas was walking with her toward the cafeteria when his phone dinged. He glanced at the screen, and immediately that soft smile slipped into place. He suddenly shot a suspicious glare her way. 

“What did you say?” 

Jess smiled. “Just that you were having a very rough day and might need a pick-me-up.” She shrugged. “I didn’t give any specifics. I left that for you.” 

Cas pulled her into a quick hug. “You’re the most amazing best friend ever.” Then he was running toward the nearest door. At the last minute he turned and called back to her, “Sign me to off-campus lunch!” 

Jess rolled her eyes, but she still swung by the office to sign him out. When she saw him before last hour, he looked a little dazed. 

“So it was a very good lunch, I’m taking it?” she murmured, and Cas blushed. 

“ _Very_ good.” 

—

For Thanksgiving, her family celebrated the day before since her dad was on-shift the day of, so she spent the day with Sam and Cas and Dean. To watch Cas, he was so happy, so bright, surrounded by this tiny self-made family that loved and wanted him. 

At the end of the day, when Sam offered to drive her home, she went to find the others to say goodbye. She found them on the couch in the den, with Cas curled tight into Dean’s side as Dean ran soft fingers slowly down his back. Both were practically asleep, so she only whispered a _goodbye_ before following Sam out the door. 

Sam came over to her house for Christmas and whispered that Dean and Cas had the Winchester place to themselves. She sighed in relief; the tension between those two was getting _unbearable_. 

For New Year’s, she and Sam went to Bela’s party. Cas stopped by for a bit, but left pretty quickly. She knew he’d gone home—well, to _Dean_ , which was one and the same for Cas— so they could watch the ball drop together. 

For Valentine’s, which luckily fell on the weekend, Dean told Sammy to send any “clients” Ash’s way, then he kidnapped Cas at the end of school on Friday and they roared off. Jess may or may not have had a hand in getting up to Cas’s room and putting together a travel bag. She felt a little bad at sneaking around Cas’s back for the secret, but it was all worth it. The next time she saw Cas, he was still glowing from the uninterrupted time with Dean.

Shortly after, Sam got some good news on an early scholarship application, a _big_ scholarship, so he and Jess convinced Dean to take a little bit of the college fund and treat Cas to a week away. A big part of her was so happy for Cas, for how much he loved Dean and received love in return, but another part of her hurt because she knew Cas was upset: his mom didn’t even _ask_ where he was going.

But then that was the last time he ever mentioned his mom, her betrayal. At some point over that trip, he'd finally realized, fully accepted even, that he had something, _someone_ , to hold to from then on. It was probably the silver band on his ring finger when the couple returned from St. Bart’s...the band that matched the one on Dean’s ring finger. 

Jess was shocked speechless, to the point that she literally could not form words. Sam had no such problem. 

“Did you get married?” he burst out, apparently just as shocked as she was. 

Cas rolled his eyes. “Engaged.” 

“Engaged for when?” Jess asked softly. “Like...this summer? 

Dean jerked his head toward the kitchen. “Let’s talk.” 

The four of them sat around the kitchen table as Dean told Sam their plans.

“You’re practically grown now, Sammy. Between your scholarships and the money already in the college fund, you’ll be pretty set.” He looked over to Cas, who beamed back at him. “Cas and I are going to Arizona for his college. I’ll be looking for a job nearby so we can save up money for whenever we decide to get married.” 

Cas looked back at them. “In the distant future, don’t worry. It’ll be the whole big ceremony with you two there, along with whoever else we want.”

Both Sam and Jess raised their hands and yelled “Best Man!” almost in unison. 

Dean chuckled. “Yeah, of course you’ll be my Best Man, Sammy.” 

Cas reached over and took Jess’s hand in his. “And you’ll be my cake cutter for the reception.” 

Jess laughed and slapped his hand away. She looked back to Sam and found him smiling widely, despite his misty eyes. She knew how big this was for him, for Dean to trust Sam with his own future so Dean could start looking out for his future with Cas. 

They agreed to keep it under wraps for the time being; there was still the last quarter of the school year to get through, but that flew by, just like it always did. 

About a week before the graduation, Jess asked Cas about his valedictorian speech. “Can I see it?” 

He blushed and glanced down at the melting ice-cream that dripped down his hand. “Um, I’m not…” he trailed off, then looked back up at her. 

Her eyebrows shot up when realization hit. “You’re _skipping_?” 

Cas smiled bashfully. “I just—I don’t care about it? As harsh as that sounds.”

“So you and Dean are just taking off, then?” 

Cas nodded, and his face was so bright, so happy. She couldn’t be upset at him, not really. It wasn’t even _her_ graduation ceremony. 

“All right,” she agreed. “As long as _I_ get to be the one to start the grapevine.” 

Cas laughed, already nodding in agreement. 

So, on the morning of graduation, when Sam picked her up to drive to the ceremony, she looked at him imploringly. 

He chuckled. “Yeah, they took off a little while ago.”

She yanked out her phone and typed out the text: _Ruby, oh my god...you’re not gonna believe what Cas and Dean did!_


	4. Dean's POV

**Summary for the Chapter:**

> Nope, Dean Winchester did not do relationships. I had a good thing going with dealing: getting paid and getting laid from both teams. 
> 
> One cute guy who was...you know, a perf—nope, not perfect. Just nice or...okay. Yeah, that was it: one cute guy who’d kissed okay didn’t change anything.
> 
> Fine, so it was clear: I was f*cked. There was no way I could just ignore this

**Notes for the Chapter:**

> FUN FACT: this chapter is definitely the longest...and I wrote it in first person because there was no way I could keep Dean's "voice" using third person. In fact, I'm still a little worried I may have gone a little too "soft" sometimes, but who doesn't love a soft Bad Boy? Especially Bad Boy Dean Winchester!

Growing up, it was always just me and Sammy. 

Mom died in a fire when he was a baby, so Dad turned to the bottle, and we were left to fend for ourselves. And by fend for ourselves, I mean leave me to raise Sammy and take care of the bills. Luckily the house had been in our family for years, but that only meant I didn’t have to worry about paying a mortgage. 

There were other bills, like electric and water and groceries. Plus Sammy grew so damn fast, he was constantly inhaling more food, and I just knew my hand-me-downs wouldn’t fit his giant ass for much longer. 

Then when he was in sixth grade, he won first prize in some big essay thing where he wrote about what he wanted to do with his life. Even then he knew he wanted to be a lawyer. 

I knew he was smart enough to make it happen, and he’d get himself into a good school. But I also knew, even as a ninth grader, what else that meant: more money. 

I’d already been grabbing some shifts at Bobby’s garage, but college and law school would cost a whole lot more than I could ever save from those few shifts, so I started working as much as possible and saved every little bit I could. 

And yeah, my grades started to slip, so Sam _wanted_ to help, but I wouldn’t let him. He had the brains, he’d be the one to do big things, help people. That was his job: keep his grades up for those big scholarships. 

Then Ash, one of Bobby’s guys who worked for cash sometimes, offered me a separate job, one that we _wouldn’t_ tell Bobby about. He needed some extra help, I needed more money, and I couldn’t keep going the way I was. I’d burn my ass out before Sammy even made it to college. 

I did good with dealing. I was handsome enough, charming enough...it got me in a lot of doors that had been closed before. I started dealing to the rich kids at Sammy’s fancy school, which got me into their parties, in with their hottest girls...and then in about eleventh grade, in with their hottest guys too. 

I never brought the guys to our house, never even told Sammy about them. Not that he’d care, but I didn’t want Dad to find out if he ever managed to actually stumble home. If John ever found out...he’d kick me out in a heartbeat, and then it’d be even tougher for me to look out for Sam.

I (barely) graduated high school and started working full-time for Bobby. Those paychecks went to bills and food and shit. But I was also working more for Ash. Hell, at some point, it started to feel like _he_ was working for _me_. 

Then Sam met Jess, this cute girl in one of his classes, and that was it. For weeks he mooned over her, constantly talking about how smart she was, how funny, how kind. Her blonde hair, her dimple, her laugh. 

“So just ask her out!” I yelled one evening after he’d been going on and on. 

That next week, I met Jess, and then it seemed like she was just part of our family too. She was as great as Sam had said, and what’s more, she didn’t care about my dealing. She even got Sam to pull back on nagging me about my “sleeping” habits. 

Yeah, I fuckin’ slept around. I was still a young guy with a pretty active (as in, always ready to go) libido. And for the time being, I was happy with that. In fact, I thought I would always be happy with that. 

Funny how life throws you a curveball, ain’t it?

When Brady called me that Friday afternoon and I agreed to meet him in the usual abandoned lot, I had no idea how my life would change. But then I was stepping under that bus stop, soaked from the rain, and everything slowed, because all I could see was _blue_. 

I’d been expecting some idiot, mostly because Brady had told me so—don’t ask me why I believed the one person that I knew was _absolutely_ an idiot. But I was not expecting it when those plush lips opened and that long tongue slipped out to swipe at a rain droplet before tossing out the challenge: “Now don’t go promising that...I might want you to try a thing or two.”

And dammit, I was a goner. Cas had me right from the start as I drove him home, loving the blush that would creep up his neck even as he threw out another sarcastic jab.

But despite that sharpness that had sucked me in, I learned that he could be so damn soft too. He made such pretty sounds when I had him under me in my backseat, gasping as I slid my tongue against his, moaning as I nipped at his neck, begging me for more.

Usually I’d go all the way, one and done. It was pretty well known that Dean Winchester did _not_ play the long game. Yet even as he gasped and moaned and breathed my name, something about his behavior made it clear that sex wasn’t happening. 

Not yet, not in the backseat of my car.

Without saying a single word, he drew a plain line: if I wanted more, I’d have to earn it. And even as I watched him run to his house, I was already grinning, planning my next step.

—

Later that evening, when I was back home, my body somewhat recovered from Cas’s drugging kisses, I realized how dumb I was acting. Like some little girl with her first crush! 

And nope, Dean Winchester did not do that. I had a good thing going with dealing, getting paid and getting laid from both teams. One cute guy who was...you know, a perf—nope, not perfect. Just nice or good or something. Yeah, that was it: one cute guy who’d kissed _okay_ didn’t change anything.

But two nights later, Jess was over doing homework with Sam. She was just as smart as him, probably more, so she was taking a senior AP lit class. Ok, yeah, she was way smarter than my genius brother. 

She mentioned Cas’s name _once_ , barely in passing, and everything in me jerked to attention. I knew I should play it cool, just walk away and text one of my usuals, but I couldn’t...not when I could learn more about _Cas_. Not when I could talk to someone about that gorgeous guy who’d been exactly what I wanted: sharp and funny and smart out of bed (or in this case, backseat), but so soft and pretty and hungry in it...not that I told her anything about any of that. 

By the end of our chat, it was clear: I was _fucked_. There was no way I could just ignore this. 

So the next day, I was in that school parking lot when the dismissal bell rang. I watched from my car as masses of students burst from the front doors, most of them too hurried to even notice me parked near the back of the lot. And even if someone saw me, they pretended they didn’t. No one wanted to be seen with their dealer here in broad daylight.

Within ten minutes, the crowd thinned out, then dropped to a trickle, but I still hadn’t seen him. What if I’d missed him somehow? But then the door was flying open again, and there he was, walking with some tall, thin blonde guy who wore a blazer, and what kind of high school student wore blazers? 

They were talking about something, with the guy waving his hands around and Cas nodding along, but then he glanced over in my direction. He paused, a tiny smile rising to his lips when I waved.

He said something to the guy walking with him, then turned and started walking towards me. The guy looked at me, then froze, his eyes wide. I don’t know what he thought was happening, but he quickly turned away and started trotting towards one of the few cars still in the lot. 

Yeah, unless I was sleeping with them, most people only saw one side of me. You know, the side that _encouraged_ them to look away and never say a fucking word. I had to cultivate that image if I wanted to be successful, or just, you know, avoid a record. 

When Cas was close enough, I reached across and opened the passenger door for him. “Wanna ride home?” 

He tilted his head to the side, a little smile tugging at just the edges of his mouth. “Depends…”

“On?” 

“Are we going to make any stops along the way?” He said it casually, but I could see the need in his eyes. 

“Definitely,” I promised. 

We _did_ make a stop on a little side street that was practically abandoned, where we ended up in my backseat again. This time we took it just a little further as he helped me get his shirt off him. He ended up with bruises all across his chest, down his torso to those sharp hip bones, clear across to the dark trail of hair that had me aching to get his pants open. But he had that line, just like before, and I was somehow _more_ excited that he didn’t let me go further than that yet, that he was making me chase it. 

Which doesn’t make sense, right? Before that, I didn’t think anything could be better than good ol’ sex. Cas was showing me, somehow without a single word, that there were better options.

We made another stop on the way home, this time to a drive-in burger joint. We grabbed a couple burgers for dinner then parked at the very back of the lot and talked for almost two hours. 

I finally dropped him off close to 7 then drove myself home...only to find Sammy sitting in the living room, his expression uncomfortable. 

“What’s up?” I asked. 

“So, um...you know how Jess goes out for a run every evening?”

“Yeah, her whole ‘communion with self’ thing,” I replied. At first I didn’t get her whole running shtick, but then she compared it to how I felt under the hood of a car, and it made sense.

“Well, she uh...she saw something today…” he hedged. 

I rolled my eyes. “Good for her.”

“She saw _you_ ,” he blurted, and that froze me in place. 

I tried to keep my expression flat. “Okay.” 

“You know, it’s okay if you like guys,” he said. “I mean, if you wanna exper—”

I rolled my eyes again and held up a hand. “Sammy, I’ve known I liked guys for a couple years now, so no experimentation needed.” 

His gaze narrowed. “Since when?”

“My junior year.” I shrugged, but blushed. “Well...I guess there’s some experimentation.” 

He arched a brow, and I dropped onto the couch next to him. “I actually _like_ Cas, like beyond just sex. He’s really smart and funny and sarcastic, but then he’s not when we’re makin…” I trailed off at Sam’s uncomfortable expression. “Sorry.” 

“So your experimentation is that you’re actually going to date a guy for the first time?” Sam guessed. 

I shook my head. “It’s that I’m trying to date _anyone_ for the first time.” 

He smiled. “That’s awesome, man! I’ve only talked to Cas a couple times, but he seems really great.” 

“Yeah,” I ran a hand over the back of my neck. 

“So when’s your next date?”

“Uh, we haven’t actually...like, called it dating or anything. We’ve just hung out and did some… uh, _stuff_ a couple times.” 

“Okay,” Sam said. “So you should probably talk about that.” 

I frowned. “You think so?” 

“Um, _yeah_.” His tone was sarcastic enough for me to glare. “Look, most people aren’t mind readers, so if you want to _date_ him, you need to be up front with that.” 

“Up front,” I muttered, nodding my head. I could do this, right?

—

Turns out being “up front” was harder than I thought. How the hell do people even approach that kind of talk? So I decided to start with baby steps, like actually bringing him around the house instead of spending all our time in the backseat of my car. 

The next Tuesday evening, Sam was over at Jess’s place for dinner with her family, so it was me and Cas, laid out on the couch in the basement. The TV was going in the background, but neither of us were watching. How could I watch some dumb show with him settled so perfect on top of me, moving his hips like that? 

“When you gotta be home?” I asked between kisses.

He rolled those blue eyes of his. “They don’t care.”

It was the same way I talked about John, but that didn’t make sense. John was a fuckin’ alcoholic who I hadn’t seen in months. Cas’s parents were some of those church people who were _way_ into the whole Jesus thing. 

“How?” I asked. “How can they not care?”

“Because if _I_ don’t exist, then neither does Naomi’s first husband. You know, my dad.”

I’d cupped his jaw to angle it where I needed as I’d reached up for another kiss. “You exist, Sweetheart.” I grinned. “Right here with me, you exist.” 

I meant it to be teasing, but suddenly it wasn’t. This look came into his eyes, and I’ll always remember it, cause it made me feel invincible, like I could do everything and anything he needed. 

He looked at me like I’d hung the fucking moon itself, and I knew that I would do _anything_ to see that look again. 

—

“You think you’re so cute, don’t you?” I growled as I jerked Cas’s jeans open and shoved my hand inside. 

“I thought it was hilarious,” he replied, more gasps than words. I bit low on his neck, low enough for him to hide, and he keened loudly. His hips seemed to move on their own as he bucked into my hand. “Is this my punishment then? I really was expecting more, since I did just give Brady a free look at your dick.” 

I laughed low. “Nah, we don’t have time for that tonight. You gotta get back to your friends.” And then I pulled my hand out and zipped up his jeans. 

He gaped at me, obviously frustrated. “Seriously, Dean?” 

“Don’t worry, Sweetheart, I’ll finish you up next time.” I gave him one last peck on the lips then pushed him out from under the bleachers, just like he had to me.

—

I was feeling pretty damn smug about the whole thing, sure that I’d ended up with the upper hand. 

Not that it was a competition, but Cas was just so goddamn _smart_. He held the top spot in his class, and he’d already gotten scholarships and early acceptance at all his top picks. So it didn’t make sense for him to be with me, a drug dealer who’d graduated by the skin of my teeth, going nowhere. 

The only thing I could figure that kept him coming back was the sex, even though we hadn’t gone “all the way” yet. I _had_ to make it good, keep it exciting for him until the emotions caught him like they’d caught me. 

And, in my mind, that meant keeping the upper hand for sex. Yeah...upper hand, my _ass_. 

That smug feeling lasted for about two days. First Cas begged off for homework, which wasn’t too weird. Like I said, he’s super smart. 

But then he said he had a thing with his parents, and that _was_ weird. Cause Cas didn’t talk to his parents... _at all_. I’ve already told you about that whole thing. 

So if Cas was saying he had a thing with his parents, it was obviously a ploy to avoid me. And that was only confirmed when I texted him the next night, and he begged off because his dog was sick. 

I couldn’t even go talk to him without seeing his parents, possibly outing him. Even if I could go, what would I say? 

_I know you’re so much better than me, and this was just sex, but can you please just come back and stay with me forever?_

God, that’s pathetic. But even that pathetic, I knew that if it had the slightest chance of working...I’d do it in a heartbeat. 

—

When Jess told me about what she’d overheard in class, how fucking _hurt_ Cas had looked all week, it was heartbreaking. A whole week he’d walked around thinking that what we had wasn’t real. A whole week that could’ve been avoided if I’d just done what Sam said and been open with him. 

I realized immediately what this was: another chance. A chance to find Cas and lay it all on the line, like I should’ve done weeks ago. 

I spent the first half of Charlie’s party stalking around, hoping to find Cas in the crowd. Then Charlie dragged me into the kitchen to meet some dudes from her LARP group, who also did some side stuff as ghost hunters or some shit. I stood there smiling and laughing, pretending I was listening when I was really watching the doorway, hoping I’d catch sight of him. 

I still almost missed him. I glanced over to the door just in time to see Cas walking away...away from _me_. I pushed my own hurt down, because I knew from what Jess had said that he was hurting too. 

I ran from the kitchen, leaving Charlie’s friend mid-sentence. 

—

I knew I wasn’t playing fair when I straddled him like that, but I needed him to listen to me, to look right into my eyes as I murmured, “I feel like...I feel like you’re it for me.” 

After, with my _boyfriend_ tucked back against my side, I pressed my lips against his temple. 

“I’m so sorry I didn’t come see you,” I whispered. “But I thought…” I trailed off with a sigh. 

“You thought what?” 

“I thought you’d realized how much better you are,” I admitted. 

His eyebrows lowered, like they did when he was trying to work through a difficult math equation. It was just as adorable. “Better than what?” 

“Better than, you know…” I couldn’t look at him. “I mean, I’m a dealer, not really going nowhere.” 

And now it was his turn to straddle me, forcing me to look into his eyes. 

“You are the most wonderful man I’ve ever met, Dean Winchester, and I adore you.” Then he grabbed me by the collar and dragged me up into another kiss.

—

Only a few weeks later, the week before Thanksgiving, I got a text from Jess, who was practically attached to the hip with Cas after the almost-breakup debacle. 

_Cas is having a really bad day_ ,she texted. 

_What? Why???_

_Take a guess_ , she responded. 

_Man!_ I fumed, my fingers flying over the screen. _Fuck that woman. How the fuck can she just ignore him?_

_I know. I think that he might need to spend lunch with someone who doesn’t ignore him?_

_I’ll be there_ , I promised. 

So, at noon on the dot, I was in the school parking lot, leaning on my car. 

_Come outside?_ I texted. _I’ve got burgers._

Two seconds later his reply came through: _be right there._

Only another minute, and the side door to the gym burst open as Cas came flying out. 

I laughed as he launched himself at me and wrapped him up in a tight hug. He leaned his weight into me, and warmth rushed through my chest at how clingy he was being. 

I loved Clingy Cas.

“Come on,” I said. “Let’s get somewhere quiet.” 

We parked in the employee lot behind the abandoned Kmart and dug into our burgers as we talked about our mornings, me at Bobby’s, him at school. But when we’d finished eating, I pulled him into my lap and let him snuggle close. 

I didn’t ask about Naomi, just let him decide on his own if he wanted to talk about it. 

“Naomi and Chuck are going out of town for Thanksgiving,” he finally whispered. “She didn’t even ask me to go. I mean, kinda but not really.” 

“What did she say?” I tried to keep my voice level. All I wanted to do was punch that hag in the face, but he didn’t need that angry side of me right now. 

I could hear his shaky breath as he whispered: “She said ‘You’re fine here, right?’”

I ran a soft hand down his spine, then back up into his hair. He still needed silence, so I pressed my nose into his temple and brushed a soft kiss across his forehead as I felt him shaking with his quiet sobs. 

“Just let it all out, Sweetheart,” I crooned. 

God, before Cas, I _never_ would’ve been this soft. I’d never really known how to care about how my partners felt. I would’ve pretended to listen as they complained, maybe hum once or twice as I pulled off my clothes and yanked them to the bed, but that was it.

Now with Cas in my lap, practically burrowed into my front, I couldn’t imagine doing anything else. I _had_ to make things better for him, because if he wasn’t good, then I sure as hell wasn’t either. 

When he finally looked up at me, I smiled reassuringly. “She’s right, you know. You’re gonna be just fine with me, Sweetheart. You, me, and Sammy...and probably Jess.” 

And his smile was back, teary but still lighting him up from the inside. “Really?” 

“Promise,” I whispered then bent to seal it with a soft kiss. He didn’t hesitate, just grabbed me as tight as he could and turned it into a hungry, desperate thing that took as much as it gave. 

When I dropped him back at the school, barely in time for his next class, his neck had more than a couple new bruises, his hair stuck up at crazy angles, and his eyes had that glassy, dazed look. 

I really should think up a better name for that look than the “I just got an awesome blowjob from my boyfriend” look.

—

Sam got invited to Jess’s for Christmas, which was great since I wouldn't have to deal with their cute couple bullshit all day. It was a little more bearable now that I had Cas, but still... 

I knew Dad wouldn’t be joining me, since I’d heard from Rufus that he was in lockup again. I almost asked Cas, but I decided I’d let him figure out what he wanted to do. There _was_ a part of him that wanted to reconcile with Naomi, and if that was what he wanted, I’d just make other plans to celebrate with him. 

About a week before, he came over to cook dinner with me while Sam and Jess worked on their trig at the kitchen table. 

“Next we add the lime juice,” he murmured, handing me the lime. Suddenly he looked up from his phone, “We’re doing Christmas here, right?” 

He said it like it was a done deal, that me and him would be spending the day together. 

“Sure,” I replied. “Where else?” 

“Well, I didn’t know if you wanted to go to Bobby’s or Ash’s place.” 

“Nah.” I winked. “I wanna stay right here with you.” 

“It’s a plan.” He looked back down at the recipe on his phone. 

I leaned down and nipped his ear. “Sam’s spending the day at Jess’s, so it’ll be just us... _all day_.” 

Man, he managed to blush so innocently, like you’d expect a good-boy valedictorian to do. But even that little blush was nothing compared to later that evening when, as I drove him home, he turned to me and murmured “I wanna do it, Dean… you know, when we have the house to ourselves.” 

And thank every god out there that we’d been stopped at a light, because I would’ve crashed the damn car with the way my hands jerked. I turned to look at him wide eyed, and he smiled through the blush.

I told you all before, I’m not new to the game. But goddamn if that shy little smile of his didn’t completely undo me. 

I turned the car into the next empty lot I could find and dragged him to me, claiming his mouth. 

“Are you sure?” I whispered when I finally let him pull away. He nodded, so eager but nervous. I pulled him into a softer kiss then whispered, “I’ll take care of you.”

On Christmas Day, we did the usual: opened gifts, cooked a nice dinner, then watched some specials on TV. But when the end credits for A Christmas Story rolled, he looked up at me and whispered, “I think we should get to bed…”

I took it slow at first, kissing over every inch of soft skin, opening him up with lubed fingers, dragging him to an orgasm with nothing more than my lips and tongue. After, as he shuddered his way down, I sucked fresh bruises into his inner thigh. 

“You ready?” I whispered. 

“Get inside me,” he gasped, and I chuckled. 

I rolled the condom on and lined up, then began pressing in slow. His blue eyes, already so dilated, rolled back in his head. 

“ _Dean_!”

—

At fucking three in the morning, my phone buzzed and jerked me from sleep. I squinted, trying to focus on the name: Bag of Dicks. I groaned. _Fucking Brady_. 

“What the hell, man?” I bit out.

At some point Cas woke up, growling in irritation at Brady’s whiny voice he could hear from the phone. When Brady offered quadruple, Cas reached over to tap my chest. 

“That’s a lot of money, Babe.” 

My brows arched as I mouthed, “You sure?” 

He nodded and sat up to start pulling some clothes on. 

“Fine, meet me at the parking lot in fifteen,” I barked at Brady. I spotted my boxers over by the dresser and pointed at them. “Hand me my boxers, Sweetheart.” 

Cas arched a brow and reached for the boxers, but instead pulled them up his own legs. 

Brady said something, but I didn’t care anymore, just gave a final warning: “If you’re not there at 3:17 on the _dot_ , I’m coming back home, and you’ll still owe me the quadruple.”

“You don’t mind if I borrow these?” Cas asked as I hung up the phone. I reached for him and yanked him back against my chest to claim a kiss. 

“And just what am I supposed to wear?” I mumbled against his lips.

He tilted his head to the side, smirking. “Guess.” 

Turned out to be a good call on his part. It was just one less piece of clothing I had to yank off when we fucked in the backseat of the Impala after Brady left. 

After, with the sweat cooling on our skin, I grinned at him. “So, I feel like we can splurge on some breakfast, right?” 

And that’s how we ended up at Denny’s at four in the morning on the day after Christmas, smiling at each other over pancakes. 

—

“You didn’t have to rush back,” I assured Cas as he curled tight against me to make sure the blanket could wrap snug around both of us. “You could’ve stayed at Lillith’s party.”

He looked up at me through his lashes. “Of course I had to come back. I wanna get my kiss at midnight.” 

I smirked and dipped for a quick peck then went back to watching the Times Square celebration. Only five minutes left to the ball drop. 

“Do you have any New Year's resolutions?” he asked. 

I avoided his gaze and stared at the TV. Did I wanna tell him? What if it ended up not working out...

“Dean?” 

I looked down to find his big blue eyes staring up at me, so trusting and patient. Why was I suddenly so nervous to tell him? This was Cas, _my_ Cas who'd given himself completely to me. 

“Um...I was kinda thinkin’ about, uh, gettin’ out of the game. You know...going legit.” I looked back at the TV, fully aware of the flush staining my neck and cheeks. 

Cas reached up to cup my cheek, turning my face down so he could look into my eyes. “If that’s what you wanna do, then that’s what we’ll do.” 

I smiled at the simplicity of his statement, at the way he made it about _us_ , not just me. I wanted it, so we’d get it done. 

“It’s just...I got some money saved up for Sammy now.” 

“Sure, _some_ ,” Cas muttered with a roll of his eyes.

I chuckled and shrugged. “With the scholarships he’s getting and stuff, I can let him take things over for himself, you know?” 

“You know that’s what he wants,” Cas reminded me. We’d talked about it before. 

“Yeah, I think that’s why it’s so easy for me to move on.” I reached down to nudge his nose with mine. “What about you?” 

“What about me?” He chased my lips, but I ducked away. 

“Any New Year's resolutions?” I prompted. 

His smile was so soft and sweet. “I just want to be as happy as I am right now, right here with you.” 

“Yeah?” I teased, but my heart was soaring. “I make you happy?” 

His face grew serious, but even then I could see the contentment in his eyes. “Before you, I was so angry,” he whispered. “about moving here, about Chuck, about my mom...I just felt invisible.” His smile came back. “And then one time, before we were even dating, you told me I exist.” 

I nodded, easily recalling that night on the couch in the basement. The fact that I brought him home, risked _John_ finding us, it proved that even then, at the very start, I’d been a goner on Cas. 

“And every day since then,” he continued, “you’ve _seen_ me, and I can’t think of a single thing that could make me happier than having the man I love see me.”

The crowd on the TV started counting down from 10, but we didn’t care. Our lips were already locked by the time that ball dropped. 

—

“So,” Ash clapped me on the back as he sat next to me in the break room. “What are you and your fella doing for Valentine’s?”

I shrugged. “Probably dinner, someplace special.” 

“Dean-o!” He cried. “Ya can’t do that! It’s so _cliche_.” 

My brow arched. “You got any other suggestions?” 

“Sure as hell do,” he nodded. “You should take him to a nice little secluded spot, just the two of you for the entire weekend.”

I rolled my eyes. “Ok, I’m sure there are plenty of available spots _three days_ beforehand.”

He reached into his pocket and tugged something out, then tossed it at me. I caught the keyring with its single key “Me cabin is su cabin, compadre.”

“You have a cabin?” 

“My uncle left it to me,” he explained. “It’s good for doing that communion with nature shit, but it’s still pretty fancy. Electricity, back-up generator, plumbing.” 

“And you’re just gonna let us use it?” I checked. 

“Hell yeah!” He winked. “Just make sure you change the bedding after.” 

Jess, who’d been to Cas’s house a few times for studying, agreed to help out. When Cas was doing his after-school stuff on Thursday, she managed to talk her way past Chuck, then grabbed some toiletries and clothes and shoved them in a bookbag. 

When the dismissal bell rang on Friday, I was waiting outside the side door that nobody used, where Balth had agreed to lead Cas. No sooner had Cas’s eyes met mine, he was running towards me.

“What are you doing here?” he asked after we’d kissed hello. 

“I’m here to kidnap you,” I teased. 

“Kidnap me?” 

“Got some big plans for our Valentine's Day,” I promised. 

“Awesome,” he breathed, then paused. “What about my clothes?” 

“Jess took care of it,” I answered. 

“And what about Naomi?” 

I nodded toward Balth, the blonde guy I’d seen with Cas that first time. “He’s got it covered.” 

Cas turned to look at his friend, who smirked at him. “Me and Crowley got it all worked out. You just have yourself some fun!” 

“You’re the absolute best, Balth!” Cas called as he ran around to the passenger side, and then we were pulling away, headed for the interstate. 

I knew I was in love with Cas, I’d told him so as we cuddled in my car during that surprise lunch date, and he'd told me at Christmas. But sitting in the Impala with him, listening to him sing along with the radio, watching him laugh at my stories, feeling his hand in mine...I knew I wanted this forever. 

It wasn’t time for that conversation yet, not when I’d just realized for myself. But right then was when my plan started forming in the back of my mind. But that’d have to wait. 

This weekend was all about Cas, about spending every possible second worshipping him with my mouth on his, my fingers on his skin, my name on his lips. But it wasn’t just about him, I realized, because I found myself crying out his name just as loudly, feeling his fingers dig in just as deeply, riding him to orgasm just as frantically. 

It was, for those couple days, just us. The rest of the world didn’t seem to exist anymore. It was me and Cas, completely caught up together, and that was fucking perfect. 

—

“I got it!!” Sammy yelled as he waved a letter in my face. “I got the scholarship!” 

“Awesome, man!” I clapped him on the back. “And you were all worried.” 

He rolled his eyes and tried to mumble something about “Not _that_ worried,” but I’d been there to watch him pace the house more than once. I let him off the hook though, since Jess was there. 

She clung to his arm as she read the letter over his elbow, then turned to me. “You know, this scholarship means that Sam’s pretty well covered.” 

“Hell yeah,” I agreed, trying to tamp down the relief in my voice. 

“Soooo,” she drew out the word, “you should take some of that money you’ve been hoarding away for Sam’s tuition and do something with Cas for spring break!” 

“Yeah!” Sam agreed, almost _too_ quickly, like they’d planned this beforehand. Cas and I had done the same to them a couple times though, so it was pretty fair. 

I thought about the velvet box hidden in the back of my dresser. I’d been trying to think of something special for asking him, and now an idea presented itself. I could take Cas somewhere nice for a few days.

St. Bart’s popped into my head, but that was more because Brady had been bitching about it the last time we met up. But it did sound nice, from what I’d heard. So I kidnapped Cas again. 

For the entire week, I had that box in my pocket, but it just never felt right. Not on the white beaches, not at the pricey restaurants, not in the red-roofed capital or the crumbling ruins. But on our last night, as Cas followed me to orgasm after orgasm, I looked right into his blue eyes, and I suddenly knew it was the right time.

And yeah I rambled some, but still he whispered, “ _Just ask me_ ,” and his smile filled me with enough confidence to finally ask: “Will you marry me?” 

We returned home wearing our matching bands. 

—

Sam stared at the rings, his mouth opening and closing, then opening again.

I winked down at Cas, who rolled his eyes and ruined my fun by telling them we were wearing _engagement_ rings. 

Finally, I told Sammy the plan, the one that had been forming in the back of my mind since Valentine’s: move to Arizona for Cas’s schooling then get married when the time was right. Sam nodded happily, because as Cas had reminded me, it _was_ what he wanted for me, to go on with my future. 

Either way, it was a lot easier to convince him about the plan than it had been with Cas. 

Yeah, Cas had said yes right away, but the whole thing about moving with him...he didn’t want me doing it just for his sake. And I'd anticipated that he'd assume I wouldn’t want to stay with him just as much as he wanted me to stay, so I reminded him of our New Year’s conversation about my plan to stop dealing. 

Finally he agreed that moving away was the best way to make that happen. So we’d made the call on the flight home from St. Bart’s: we’d move to Arizona together, get an apartment somewhere near campus, and then someday get married when we were ready. And then he’d spent the rest of the flight staring up at me with those star-struck eyes, the same ones he’d given me on my basement couch way back at our beginning. 

He finished out his senior year, keeping his engagement ring on a chain around his neck while at school and around his friends. Only Sam and Jess knew, and they’d been sworn to secrecy until after we left, which was the morning of graduation. Apparently Cas wanted to skip, and I wasn’t about to argue with him...cause he wins most of our arguments anyways. 

Now we’re settled in Arizona, have been for a few years. 

I still have the job I got at the garage when we moved, but I’m saving up for my own place that will focus on auto detailing. I’ve already created a bit of a name for myself just working out of our garage (yeah, we decided to move to an actual house last year), and I’m taking business classes at ASU. 

Cas is about to go into his senior year, still top of his class. And because he’s just so fucking smart, he’s already gotten two job offers. Both of them are pretty good, but he wants to hold out on a definite answer, cause he’ll probably get some that are even better this year. 

Every step we’ve taken forward, every time we’ve ended up on a new path, we’ve stuck together. Yeah there were tense moments, and more than once I wondered (and I know he sometimes wondered too) if we’d made the right choice about moving in together so young. But those times passed and left us stronger.

We’re still crazy about each other, and I know we always will be, no matter what else life might bring our way in the years ahead. But before all that...I think it’s about time for us to plan a wedding.

**Author's Note:**

> I've had this idea floating in and out of my head for a while now, so I figured I'd finally write a short little thing just to get it off the plate.
> 
> And then I wrote another short little thing from Cas's POV
> 
> And then I wrote another short little thing from Jess's POV
> 
> And then I had people asking for Dean's POV, so I wrote a longer chapter for him.


End file.
